220130-39-2Relevant academic research and scientific papers
Reactions of tetracyclic tetraaminophosphoranes with dichloroperfluoro cyclic and acyclic alkenes and halo compounds
Gupta,Kirchmeier, Robert L.,Shreeve, Jean'Ne M.
, p. 147 - 151 (1998)
Cyclenphosphorane was reacted with 1,2-dichlorotetrafluorocyclobutene-1, 1,2-dichlorohexafluorocyclopentene-1, 1,2-dichlorooctafluorocyclohexene-1, iodopentafluorobenzene, 2-iodo-1,1,1-trifluoroethane, and 2,3-dichlorohexafluorobutene-2 in the presence of triethylamine at room temperature in tetrahydrofuran to form monochlorotetrafluorocyclobutenylcyclenphosphorane, monochlorohexafluorocyclopentenylcyclenphosphorane, monochlorooctafluorocyclohexenylcyclenphosphorane, pentafluorophenylcyclenphosphorane, 1,1,1-trifluoroethylcyclenphosphorane, and 2-chlorohexafluorobut-2-enylcyclenphosphorane in 70-80% yields, respectively. Cyclamphosphine oxide reacted with dichloroperfluorocyclic alkenes in the presence of triethylamine in chloroform to form N-(chlorotetrafluorocyclobutenyl)cyclamphosphine oxide, N-(chlorohexafluorocyclo-pentyl)cyclamphosphine oxide and N-(chlorooctafluorocyclohexenyl)-cyclamphosphine oxide in ~50% yields, respectively. These moisture sensitive cyclamphosphine oxide derivatives are stable and are soluble in CHCl3, CH3CN and DMSO.
Synthesis of cyclenphosphoranes with polyfluorophenyl substituents; An X-ray structure of N-methyl cyclen-p-(heptafluorotolyl)phosphorane
Gupta,Kirchmeier, Robert L.,Shreeve, Jeanine M.
, p. 223 - 228 (2007/10/03)
The metathesis reactions between the lithiated derivative of cyclenphosphorane (2) and octafluorotoluene, hexafluorobenzene, pentafluorobenzonitrile, pentafluoronitrobenzene, pentafluoro-n-butylbenzene, pentafluorobenzene and p-(cyanotetrafluorophenoxy-pentafluorobenzene) under reflux conditions gave cyclen-p-(heptafluorotolyl)phosphorane (3), cyclen-p-(pentafluorophenyl)phosphorane (4), cyclen-p-(cyanotetrafluorophenyl)phosphorane (5), cyclen-p-(tetrafluoronitrophenyl)phosphorane (6), cyclen-p-(n-butyltetrafluorophenyl)phosphorane (7), cyclen-p-(tetrafluorophenyl)phosphorane (8) and cyclen-p-(p-cyanotetrafluoro-phenoxytetrafluorophenyl)phosphorane (9), respectively, in good yields. All products were characterized by spectral and analytical techniques. These materials are moderately stable thermally but are moisture sensitive, hydrolyzing to form cyclen phosphine oxide (10). Addition of CH3I to 3 affords the phosphoammonium iodide (11). The X-ray crystal structure of 11 was obtained. The crystal is triclinic with a space group P1. The unit cell parameters a=7.8652(2) A, b=8.584(2) A, c=22.1573(3) A; α=80.9010(10)°; β=79.2490(10)°; γ=76.9930(10)°; and Z=2.
